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| Other Sizes |
| Targets |
Phage display screening studies have identified chromogranin B and glutaredoxin 3 as direct binding proteins of neoechinulin A, with the compound exhibiting high affinity for both targets . Chromogranin B is a plausible target mediating the compound's neuroprotective effects, as RNA interference-mediated depletion of chromogranin B decreased the sensitivity of PC12 cells to SIN-1-induced cytotoxicity . Additionally, neoechinulin A inhibits the NF-κB and p38 MAPK signaling pathways, thereby reducing the production of pro-inflammatory mediators including iNOS and COX-2 in LPS-stimulated macrophages . In the context of antioomycete activity, the compound disrupts energy metabolism by affecting glycolysis/gluconeogenesis, pyruvate metabolism, and glutathione metabolism .
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| ln Vitro |
In a dose-dependent manner, neoechinulin A (RAW264.7 macrophages; 3 hours; cells then stimulated with LPS (1 μg/mL) for 18 hours) decreases the production of PGE2, TNF-α, and IL-1β[2]. Pro-inflammatory mediators and cytokines such as NO, PGE2, TNF-α, and IL-1β can be inhibited by neoechinulin A. Additionally, it inhibited the NF-κB and p38 MAPK signaling pathways, which decreased the production of iNOS and COX-2 in LPS-stimulated RAW264.7 macrophages[2]. Neoechinulin A prevents PC-12 cells from being harmed by inflammation by inhibiting the activation of microglia caused by amyloid-β oligomers[3].
In vitro studies have demonstrated that neoechinulin A exhibits potent neuroprotective activity against various neurotoxins. In SIN-1-induced neurotoxicity models, the compound showed an IC50 of 40 μM, protecting PC12 cells from peroxynitrite-mediated damage . Against rotenone-induced Parkinson‘s disease models, the compound demonstrated an IC50 of 100 mM . For anti-inflammatory activity, neoechinulin A (12.5-100 μM) dose-dependently reduced pro-inflammatory mediators including NO, PGE2, TNF-α, and IL-1β in LPS-stimulated macrophages, with an IC50 of 12.5-100 μM . The compound also exhibits antioomycete activity against Phytophthora capsici with an EC50 of 21.95 μg/mL . |
| ln Vivo |
Neoechinulin A (300ng/mouse, icv) was administered prior to the intracerebroventicular (icv) administration of LPS (10 μg/mouse), which prevented the significant decrease in spontaneous alternation behavior in the Y-maze test[1].
In vivo studies have confirmed the pharmacological efficacy of neoechinulin A in animal models. In a mouse memory impairment model induced by intracerebroventricular LPS administration (10 μg/mouse), pre-treatment with neoechinulin A (300 ng/mouse, icv) prevented the significant decrease in spontaneous alternation behavior in the Y-maze test, indicating improvement in memory function . In antioomycete studies, in vivo assays demonstrated that neoechinulin A effectively inhibited Phytophthora capsici infection and enhanced the protective capacity of pepper plants . The compound also induced antidepressant-like effects in behavioral studies . |
| Enzyme Assay |
Direct binding assays for neoechinulin A target identification employed phage display screening technology . In this protocol, a phage display library is incubated with immobilized neoechinulin A to isolate phages displaying peptides that bind to the compound. After several rounds of biopanning, positive clones are sequenced to identify candidate binding proteins. Quartz crystal microbalance (QCM) analyses are then performed to determine binding affinity, using purified recombinant proteins (chromogranin B or glutaredoxin 3) immobilized on the QCM sensor chip. Varying concentrations of neoechinulin A are injected, and the frequency changes are recorded to calculate association and dissociation rates. This method has confirmed that neoechinulin A exhibits high affinity for both chromogranin B and glutaredoxin 3 .
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| Cell Assay |
Typical in vitro cell assays for evaluating neoechinulin A's neuroprotective effects utilize PC12 neuronal cells or RAW264.7 macrophages . For neuroprotection studies, PC12 cells are seeded in 96-well plates and pre-treated with varying concentrations of neoechinulin A (e.g., 0-200 μM) for 3 hours, followed by exposure to neurotoxins such as SIN-1 (peroxynitrite generator), rotenone, or 6-OHDA for 24-48 hours . Cell viability is assessed using MTT assay, and apoptosis is evaluated by caspase-3 activity measurement or Annexin V/PI staining. For anti-inflammatory studies, RAW264.7 macrophages are pre-treated with neoechinulin A (12.5-200 μM) for 3 hours, then stimulated with LPS (1 μg/mL) for 18 hours . Nitrite production is measured using Griess reagent, while TNF-α, IL-1β, and PGE2 levels are quantified by ELISA. NF-κB and MAPK pathway activation is assessed by Western blot analysis of phosphorylated proteins.
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| Animal Protocol |
In vivo studies for assessing neuroprotective and memory-enhancing effects of neoechinulin A employ mouse models . A representative protocol: Male ICR mice (6-8 weeks old) receive intracerebroventricular (icv) injection of LPS (10 μg/mouse) to induce memory impairment. Neoechinulin A (300 ng/mouse, icv) is administered 30 minutes prior to LPS injection. Behavioral testing is performed 24 hours post-LPS administration. The Y-maze test is conducted to assess spontaneous alternation behavior: each mouse is placed in the Y-maze and allowed to explore freely for 8 minutes, with the sequence of arm entries recorded. The percentage of alternations is calculated as (number of triads containing entries into all three arms)/(total number of arm entries - 2) × 100. For antidepressant-like activity evaluation, the forced swim test and tail suspension test are performed according to standard protocols .
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| ADME/Pharmacokinetics |
As a research-grade natural product, detailed ADME profiling is limited. However, based on physicochemical property predictions, the compound has a molecular weight of 323.4 g/mol, a calculated LogP value of 3.3, and a LogD value of 2.737, indicating moderate lipophilicity suitable for cellular permeation . The topological polar surface area is 74.0 Ų, and the compound has 3 hydrogen bond donors and 2 hydrogen bond acceptors . For research applications, neoechinulin A is soluble in DMSO and can be formulated for in vivo administration using co-solvent systems such as DMSO:PEG300:Tween 80:S saline (10:40:5:45) or DMSO:Corn oil (10:90) . The powder is stable at -20°C for up to 3 years and at 4°C for up to 2 years .
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| Toxicity/Toxicokinetics |
According to the Safety Data Sheet for neoechinulin A, the compound is classified as “not a hazardous substance or mixture“ under normal handling conditions . It has not been listed as a carcinogen by NTP, IARC, OSHA, or ACGIH . The toxicological effects of the compound have not been thoroughly studied, and specific LD50 values, acute toxicity, chronic toxicity, genotoxicity, or reproductive toxicity data are not available . In in vitro cell viability assays using RAW264.7 macrophages, neoechinulin A showed no significant cytotoxicity at concentrations up to 200 μM . In the context of anticancer studies using HeLa cells, the compound exhibited an IC50 of 1.25-10 μM, indicating its ability to inhibit cancer cell proliferation . The product is strictly intended for research use only and is not for human diagnostic or therapeutic applications .
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| References |
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| Additional Infomation |
neoechinulin A has been reported to have been found in Monascus purpureus, Aspergillus stellaria, and other organisms with available data.
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| Molecular Formula |
C19H21N3O2
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| Molecular Weight |
323.39
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| Exact Mass |
323.163
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| CAS # |
51551-29-2
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| PubChem CID |
9996305
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
655.7±55.0 °C at 760 mmHg
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| Flash Point |
350.4±31.5 °C
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| Vapour Pressure |
0.0±2.0 mmHg at 25°C
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| Index of Refraction |
1.628
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| LogP |
2.55
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
24
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| Complexity |
581
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C[C@H]1C(=O)N/C(=C\C2=C(NC3=CC=CC=C32)C(C)(C)C=C)/C(=O)N1
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| InChi Key |
MYRPIYZIAHOECW-SAIXKJTDSA-N
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| InChi Code |
InChI=1S/C19H21N3O2/c1-5-19(3,4)16-13(12-8-6-7-9-14(12)21-16)10-15-18(24)20-11(2)17(23)22-15/h5-11,21H,1H2,2-4H3,(H,20,24)(H,22,23)/b15-10-/t11-/m0/s1
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| Chemical Name |
(3S,6Z)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]piperazine-2,5-dione
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| Synonyms |
neoechinulin A; 51551-29-2; (3S,6Z)-3-methyl-6-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]piperazine-2,5-dione; (3S,6Z)-3-methyl-6-((2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl)methylidene)piperazine-2,5-dione; RefChem:165220;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0922 mL | 15.4612 mL | 30.9224 mL | |
| 5 mM | 0.6184 mL | 3.0922 mL | 6.1845 mL | |
| 10 mM | 0.3092 mL | 1.5461 mL | 3.0922 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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